Designer Merge To Word issue

I wish I could say Happy New Year, but I'm rather frustrated today. After FINALLY getting Designer Merge - To - Word to actually populate the templates that we created, this happens on one of my users PC. It is only affecting one machine, so far. We operate on a Windows 10, have a shared database and ACT! Version 19. I've attached a screenshot below. Any idea how to fix this issue? We have 6 other users and have not encountered this problem.

On another note - Downloading the Outlook4Act program - Is this straight forward, step-by-step process or somewhat complex? This same machine is having issues with the Outlook E-mail program communicating with ACT. ( Or vice-versa) ; It will not allow for Scheduling of Meetings on Outlook Calendar nor will it allow click-to-e-mail.